Identification
- Summary
Nonoxynol-9 is a vaginal spermicide used for the non-hormonal contraception in conjunction with other modes of contraception.
- Brand Names
- Conceptrol, Gynol II, Today Sponge, Vcf Contraceptive
- Generic Name
- Nonoxynol-9
- DrugBank Accession Number
- DB06804
- Background
Nonoxynol-9 (N-9) is a typical surfactant used as a vaginal spermicide. Spermicides are locally acting non-hormonal contraceptives. When present in the vagina during intercourse, they immobilize/inactivate/damage and/or kill sperms without eliciting systemic effects. N-9 has been in use for more than 30 years as an over-the-counter (OTC) drug in creams, gels, foams and condom lubricants. It is the most commonly used spermicidal contraceptive in the UK and the USA. In several European countries, spermicides are no longer on the market.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Nonoxynol-9 (DB06804)
- Weight
- Average: 616.8235
Monoisotopic: 616.41864814 - Chemical Formula
- C33H60O10
- Synonyms
- 26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
- Nonaethylene glycol mono(nonylphenyl) ether
- Nonaethylene glycol nonylphenyl ether
- Nonoxynol 9
- Nonylphenol octa(oxyethylene) ethanol
- P-Nonylphenyl polyethylene glycol ether
- PEG-9 nonyl phenyl ether
- Polyoxyethylene (9) nonyl phenyl ether
- Tergitol NP-9
- Tergitol NP9
Pharmacology
- Indication
Nonoxynol 9 is a surfactant spermicide used for contraception in spermicidal creams, jellies, foams, gel, and lubricants. It is also used in conjuction with other methods of contraception, including condoms, cervical caps and diaphragms.
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- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Nonoxynol-9 interacts with the lipids in the membranes of the acrosome and the midpiece of the sperm. The sperm membranes are lysed; the acrosome, neck and midpiece of the spermatozoa are loosened and then detached which results in their immobilization and death.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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The major drawback of nonoxynol-9 is its detergent-type action on epithelial cells and the normal vaginal flora. Detergent-type spermicides alter the vaginal flora, possibly leading to an increased risk of opportunistic infections. These are known to enhance the susceptibility of the epithelium of the lower genital tract to HIV and human papillomavirus infection. N-9 can cause vaginal irritation and allergic vaginitis as well as genital irritation in male partners.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The metabolism of Nonoxynol-9 can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Nonoxynol-9. Amobarbital The metabolism of Nonoxynol-9 can be increased when combined with Amobarbital. Aprepitant The serum concentration of Nonoxynol-9 can be decreased when it is combined with Aprepitant. Belzutifan The therapeutic efficacy of Nonoxynol-9 can be decreased when used in combination with Belzutifan. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Advantage 24 (Lake Pharmaceuticals) / Gynoll (Ortho Options) / Today (Bliss Pharmaceuticals) / VCF (Apothecus Pharmaceuticals)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Conceptrol Options Gel 4.0 g/100g Vaginal Caldwell Consumer Health Llc 2011-05-01 Not applicable US 
ContraSeed Suppository 100 mg/1 Vaginal International Trading Pharmaceutical Laboratories, Inc 2015-02-26 2017-03-31 US Encare Insert 100 mg/1 Vaginal Blairex Laboratories, Inc. 1999-09-01 2020-01-01 US Gynol II Extra Strength Gel 3.0 g/100g Vaginal Caldwell Consumer Health Llc 2011-05-01 Not applicable US Today Vaginal Contraceptive Sponge 1000 mg/1 Vaginal Mayer Laboratories, Inc. 1983-04-01 Not applicable US
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Alcohols
- Antispermatogenic Agents
- Compounds used in a research, industrial, or household setting
- Contraceptive Agents, Female
- Contraceptive Agents, Male
- Ethylene Glycols
- Glycols
- Hormonal Contraceptives for Systemic Use
- Macromolecular Substances
- Noxae
- Polyethylene Glycols
- Polymers
- Reproductive Control Agents
- Spermatocidal Agents
- Surface-Active Agents
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Ethers
- Direct Parent
- Polyethylene glycols
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Primary alcohols / Hydrocarbon derivatives
- Substituents
- Alcohol / Alkyl aryl ether / Aromatic homomonocyclic compound / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Phenol ether / Phenoxy compound / Polyethylene glycol / Primary alcohol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tergitol (CHEBI:53775)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 48Q180SH9T
- CAS number
- 26027-38-3
- InChI Key
- FBWNMEQMRUMQSO-UHFFFAOYSA-N
- InChI
- InChI=1S/C33H60O10/c1-2-3-4-5-6-7-8-9-32-10-12-33(13-11-32)43-31-30-42-29-28-41-27-26-40-25-24-39-23-22-38-21-20-37-19-18-36-17-16-35-15-14-34/h10-13,34H,2-9,14-31H2,1H3
- IUPAC Name
- 26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
- SMILES
- CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
References
- General References
- Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. doi: 10.1080/13625180802263515. [Article]
- External Links
- Human Metabolome Database
- HMDB0015680
- KEGG Drug
- D06490
- PubChem Compound
- 72385
- PubChem Substance
- 99443296
- ChemSpider
- 65319
- BindingDB
- 50442874
- 53750
- ChEBI
- 53775
- ChEMBL
- CHEMBL1410
- ZINC
- ZINC000008214629
- PharmGKB
- PA450648
- Wikipedia
- Nonoxynol-9
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Prevention Human Immunodeficiency Virus (HIV) Infections 1 3 Completed Prevention Pregnancy 1 2 Completed Basic Science Vaginal Infections / Vaginal Inflammation 1 2 Completed Prevention Healthy Subjects (HS) 1 2, 3 Completed Prevention Contraception 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Vaginal 4.0 g/100g Suppository Vaginal 100 mg/1 Insert Vaginal 100 mg/1 Gel Vaginal 3.0 g/100g Insert Vaginal 150 mg Sponge Vaginal 1000 mg/1 Aerosol, foam Vaginal 125 mg/1g Film, soluble Vaginal 280 mg/1 Gel, metered Vaginal 4 g/100g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000214 mg/mL ALOGPS logP 3.49 ALOGPS logP 4.82 Chemaxon logS -6.5 ALOGPS pKa (Strongest Acidic) 15.12 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 103.3 Å2 Chemaxon Rotatable Bond Count 35 Chemaxon Refractivity 169.01 m3·mol-1 Chemaxon Polarizability 77.07 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.8118 Caco-2 permeable + 0.661 P-glycoprotein substrate Substrate 0.721 P-glycoprotein inhibitor I Non-inhibitor 0.6742 P-glycoprotein inhibitor II Non-inhibitor 0.7359 Renal organic cation transporter Non-inhibitor 0.7701 CYP450 2C9 substrate Non-substrate 0.7821 CYP450 2D6 substrate Non-substrate 0.7658 CYP450 3A4 substrate Non-substrate 0.5396 CYP450 1A2 substrate Non-inhibitor 0.7665 CYP450 2C9 inhibitor Non-inhibitor 0.877 CYP450 2D6 inhibitor Non-inhibitor 0.9161 CYP450 2C19 inhibitor Non-inhibitor 0.7044 CYP450 3A4 inhibitor Inhibitor 0.5899 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9084 Ames test Non AMES toxic 0.9423 Carcinogenicity Non-carcinogens 0.8423 Biodegradation Ready biodegradable 0.7353 Rat acute toxicity 2.2394 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6776 hERG inhibition (predictor II) Inhibitor 0.5489
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 299.1899151 predictedDarkChem Lite v0.1.0 [M-H]- 308.4176151 predictedDarkChem Lite v0.1.0 [M-H]- 245.09709 predictedDeepCCS 1.0 (2019) [M+H]+ 294.6175151 predictedDarkChem Lite v0.1.0 [M+H]+ 304.5214151 predictedDarkChem Lite v0.1.0 [M+H]+ 247.96371 predictedDeepCCS 1.0 (2019) [M+Na]+ 295.5541151 predictedDarkChem Lite v0.1.0 [M+Na]+ 305.9580151 predictedDarkChem Lite v0.1.0 [M+Na]+ 255.37465 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Zalenskaya IA, Cerocchi OG, Joseph T, Donaghay MA, Schriver SD, Doncel GF: Increased COX-2 expression in human vaginal epithelial cells exposed to nonoxynol-9, a vaginal contraceptive microbicide that failed to protect women from HIV-1 infection. Am J Reprod Immunol. 2011 Jun;65(6):569-77. doi: 10.1111/j.1600-0897.2010.00964.x. Epub 2011 Jan 18. [Article]
Drug created at September 14, 2010 16:21 / Updated at June 12, 2020 16:52